Leadership Reflection: Raymond Jackson

2015 YNPN Chicago Leadership Institute Participant, Raymond Jackson


1. Tell us about your current role?

I'm the associate director of advancement for the Urban Education Institute (UEI) at the University of Chicago. At UEI, our mission is to produce knowledge to create more reliably excellent urban schooling. My role in advancement is to strengthen relationships with donors and volunteers and increase the number of individuals supporting UEI through gifts of time, talent, and financial support.

2. Why do you like working in the nonprofit sector?

Since I’ve never worked outside the nonprofit sector I sometimes forget there are people who don’t work to support organizations that address major societal needs. My entire career, I’ve been fortunate to work in higher education and see the transformation of young people and even returning adult students. I firmly believe that education is the key to positively changing our world.

3. Why did you sign up for the Leadership Institute?

I signed up for the Leadership Institute because I was looking for a well-rounded course on nonprofit leadership that would help me as I advance my career in nonprofit development. I’ve been able to learn from so many professionals in my cohort and get a better understanding of the challenges faced by all types of nonprofits. I like that my cohort members have many different responsibilities and come from various organizational types.

4. Tell us about how what you've learned in the Leadership Institute is changing or reinforcing your leadership style and helping you shape your next steps?

At a very basic level, my experience in the Leadership Institute is helping me feel more comfortable asking questions. In the past, I would spend more time trying to figure things out on my own because a small part of me felt if I asked certain questions, the perception would be that I didn’t know what I was doing. I’ve since learned that leaders ask questions. In fact, great leaders ask questions and I am beginning to understand that the ability to ask good questions is an invaluable part of leadership.

5. What have you learned from your Leadership Institute Mentor?

I struggled to develop my short term goals but have always been able to share my ultimate career goal to become a chief development officer at a small liberal arts college. My mentor helped me to identify some shorter term goals that would help reach my ultimate goal. For example, my mentor encouraged me to schedule informational interviews with three chief development officers at small colleges in the Chicagoland area to learn more about their work and the skills I will need to develop now in order to be successful in the future.

6. What is the best piece of advice you've ever received?

I’ve been so blessed to receive great advice from so many people thus far in my career. One piece sticks out more and more these days as I’ve just started a new role and am trying to make an impact on my team. When I played football in college and made the change from interior offensive lineman to tight end, I found myself making a few mistakes in practice. It was difficult at first to understand my plays. One of my favorite coaches told me, It’s alright to make a mistake as long as you learn from it. And if you do make a mistake, make sure it’s an aggressive one! Basically, coach meant if I was going to block the wrong person, make sure I block the heck out of that person! I try to apply the same principal to my career (no, not blocking the heck out of my co-workers). I know I am going to make mistakes but I try to make sure I am giving everything that I can on every single play.